• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    Process for increasing the content of phenols with biological activity in red grapes comprising an exogenous treatment with an enantiomer of methyl jasmonate diluted in ethanol. The presence of polyphenolic compounds in grapes means that their consumption has multiple beneficial effects for health. The present invention raises for the first time a simple post-harvest procedure, which comprises contacting exogenously grapes red with a jm enantiomer diluted in ethanol. The proposed method achieves the simultaneous and substantial increase of more than one phenolic compound with healthy biological activity in grapes, which are preferably polyphenols and which are more preferably resveratrol and forms of quercetin, and constitutes an alternative to the procedures using phytohormones as agents of activation. (Machine-translation by Google Translate, not legally binding)
    公开号:ES2550690A1
    申请号:ES201430520
    申请日:2014-04-08
    公开日:2015-11-11
    发明作者:Gema FLORES MONREAL；Gracia Patricia Blanch Manzano；Maria Luisa Ruiz Del Castillo
    申请人:Consejo Superior de Investigaciones Cientificas CSIC；
    IPC主号:
    专利说明:

    P201430520
    04-08-2014
    PROCEDURE TO INCREASE THE CONTENT OF PHENOLS WITH BIOLOGICAL ACTIVITY IN INK GRAPES THAT INCLUDES AN EXOGENOUS TREATMENT WITH A METHYLED JASMONATE DILUTED IN ETHANOL
    DESCRIPTION
    TECHNICAL SECTOR
    The present invention is encompassed within the food and health sectors, since it specifically refers to a method for increasing the content of phenols with healthy biological activity in previously harvested red grapes, preferably polyphenols, and more preferably resveratrol and different Quercetin forms, and comprising an exogenous treatment with a methyl jasmonate enantiomer diluted in ethanol.
    STATE OF THE TECHNIQUE
    The presence of bioactive compounds in grapes makes their consumption present multiple beneficial effects for health. Thus, its anti-inflammatory effects, its ability to prevent the development of cardiovascular diseases and diabetes, and, singularly, its anti-cancer effect are known.
    Among the bioactive compounds present in the grape, it is worth mentioning the polyphenols, starting with resveratrol, from which this fruit is considered one of the main sources and is characterized by its antitumor activity. Another polyphenol present in grapes in minor quantities is quercetin, both free and in its different forms, which also has important biological properties.
    Such are the beneficial health effects of these bioactive polyphenols present in the grape that its extract has been marketed for years as a food supplement. Similarly, there are also nutritional supplements of resveratrol and quercetin, which are supplied individually or in combination.
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    In the state of the art documents are identified that refer to procedures for increasing the content of polyphenols in plant tissues or foods through the use of activating agents.
    A frequently used activating agent is methyl jasmonate (JM) which is a phytohormone that exists endogenously in the upper plants and has multiple functions. For example, it is possible to find documents that refer to the use of JM in in vitro cultures (US7666677; Nopo-Olazabal et al., J. Agric. Food Chem. 2013, 61, 11744-11758); or to the use of JM combined with other compounds such as cyclodextrins also in in vitro cultures (WO2009106662A1).
    On the other hand, it is possible to find documents that refer to the pre-harvest application of JM on the plant to increase the content of compounds with antioxidant activity. For example, anthocyanins and flavonols that include quercetin O-glucoside in grapes (Ruiz-García et al., J. Agric. Food Chem. 2012, 60, 1283-1290); or antioxidant activity and content of phenolic compounds in blackberry and raspberries (Wang et al., Food Chem. 2008, 107, 1261-1269).
    On the contrary, other documents refer to the post-harvest application of JM directly on the fruit to increase, for example, quercetin in cabbage (Khang and Liang, Biochem & Pharmacol. 1997, 54, 1013-1018); carotenes and chlorophylls in apples and tomatoes (Pérez et al., J. Plant Growth Regulat. 1993, 12, 163-167; Saniewski and Czapski, Experientia. 1983, 39, 1373-1374); the antioxidant capacity of raspberries (Chanjirakul et al., Postharvest Biol. Technol. 2006, 40, 106-115); or to favor the biosynthesis of resveratrol in grapes (Vezzulli et al., Am. J. Enol. Vitic., 2007, 58, 530-533.).
    However, the form of JM that is mostly used in food and plant tissue treatments referred to is the stereoisomeric mixture of commercial JM, which contains 5% of (-) - and (+) - epiJM and 95% of ( -) - and (+) - JM.
    In the knowledge of the inventors there are very few documents that refer to the use of JM enantiomers in this type of treatments. See de la Peña Moreno et al. (J. Agric. Food Chem., 2010. 58, 11639-11644) which refers to the post-harvest treatment of raspberries with (+) - JM and (-) - JM; and from Peña Moreno et al. (Eur. Food Res. Technol. 2010, 231, 829-834) which refers to the use of the same enantiomers for the modification of volatile compounds in strawberries.
    P201430520
    04-08-2014
    DESCRIPTION OF THE INVENTION
    Brief Description of the Invention
    5
    An aspect of the invention constitutes a process for simultaneously increasing the content of more than one phenolic compound with healthy biological activity in red grapes comprising:
    10 a) contacting previously harvested red grapes with an enantiomer of Methyl Jasmonate (JM) diluted in ethanol.
    Additionally, the above procedure comprises the following steps:
    15 b) subject the whole of step (a) to a constant temperature of between 25 and 40 ° C for a period of time between 20 and 30 hours; and subsequently
    c) hermetically isolate the whole of stage (b) and keep it at a temperature between 4 and 10 ° C for a period of time between 0 and 7 days.
    Preferably, the JM enantiomer is selected from (-) - JM and (+) - JM and the phenolic compounds with healthy biological activity are polyphenols, which are more preferably resveratrol and different forms of quercetin. Detailed Description of the Invention
    The technical problem that solves the invention is to achieve an alternative to post-harvest treatments with hormones to achieve the increase of phenols with healthy biological activity in red grapes. The proposed procedure ensures that
    At the same time, more than one of these phenolic compounds is increased in red grapes, significantly higher than what is achieved using other hormone treatments known in the state of the art.
    The inventors have discovered that an exogenous treatment comprising putting in
    35 contact red grapes already harvested and a JM enantiomer diluted in ethanol; keep at constant room temperature for 24 hours; and let stand for 5 days at a
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    temperature of 4º C (see example 2), manages to increase the activity of the enzymes involved in the simultaneous bioforming of resveratrol and different forms of quercetin and, as a consequence, achieve a high accumulation of these phenols with healthy biological activity in the tissue of the grapes (see example 4.3). The proposed procedure referring exclusively to red grapes and the results obtained, are considered novel and completely unexpected since the few documents present in the state of the art that refer to the treatment of other fruits with JM enantiomers and with commercial stereoisomeric mixtures refer results divergent
    The main advantages of the process of the invention are listed below:
    a) allows to increase simultaneously and considerably the content of more than one phenol with healthy biological activity, obtaining a more complete functional grape;
    b) it is a simple and economical procedure since it does not require any type of technology, nor qualified personnel for its management;
    c) it is carried out once the grapes are harvested; Y
    d) the procedure is easy to implement by any industry.
    It is suggested that the activity of the activating agents in terms of increasing the activity of the enzymes involved in the bioforming of phenolic compounds with healthy biological activity, such as polyphenols, and more specifically resveratrol and different forms of quercetin, is a process specific that occurs between each activation agent and the fruit or plant tissue on which it is applied.
    Thus, for example, as recorded in the state of the art, and as can be seen in the information summarized in Table 1 on the increases in polyphenolic compounds obtained by treatment with the mixture of commercial JM stereoisomers, one would expect that its application in combination with ethanol on the ink grape would mean an increase in the concentration of the compounds comprising the present invention. However, the inventors have discovered (see example 4.3) that not only does it not produce significantly statistical changes in the content of polyphenols such as resveratrol, quercetin-3-O-glycoside and quercetin-3-O-rutinoside, but also produces a significant decrease in the content of quercetin-3-O-galactoside.
    P201430520
    04-08-2014
    Table 1. Bibliographic summary on the increase in phenolic compounds obtained by treating plant foods with the commercial stereoisomeric mixture of JM.
    Appointment CompoundPlant food or tissue
    Ruiz-García et al., 2012 Anthocyanins and flavonolsgrapes
    Wang et al., 2008 Antioxidant activity and phenolic compoundsBlackberry and Raspberries
    Vezzulli et al., 1997 ResveratrolGrape
    Khang et al., 1992 QuercetinCabbage
    Saniewski and Czaspki, 1983 CaroteneTomato
    Pérez et al., 1993 ChlorophyllsApple
    Chanjirakul et al., 1996 Antioxidant activity and phenolic compoundsRaspberries
    5 Along the same lines, de la Peña Moreno et al. (J. Agric. Food Chem., 2010, 58, 11639-11644) obtained increments of myricetin, quercetin and kaempferol in raspberries using the (+) - JM enantiomer, but did not appreciate increases when using the (-) - JM.
    These are divergent data that are presented in this document and that reinforce the
    The fact that the results obtained are totally unexpected when using the method of the invention.
    The invention relates to a process for simultaneously increasing the content of more than one phenolic compound with healthy biological activity in red grapes, which
    Preferably they are polyphenols and more preferably resveratrol and quercetin forms, hereinafter process of the invention, which comprises contacting previously harvested grapes with a JM enantiomer diluted in ethanol.
    Preferably, the JM enantiomer diluted in ethanol is introduced into a vial, and subsequently converted into steam that contacts the grapes.
    Also preferably, the JM grapes and enantiomer are introduced into a container that has a volume such that 2/3 of the container is occupied by the red grapes and 1/3 is free to allow vaporization of the JM.
    P201430520
    04-08-2014
    The process of the invention is optimized when the following steps are carried out immediately after contacting previously harvested grapes and the JM enantiomer diluted in ethanol:
    b) the previous set is subjected to a constant temperature of between 25 and 40 ° C for a period of time between 20 and 30 hours; and subsequently
    c) said assembly is hermetically isolated and maintained at a temperature between 4 and 10 ° C for a period of time between 0 and 7 days.
    In the present invention, "phenols or phenolic compounds with healthy activity" means organic compounds whose molecular structure contains at least one phenol group and which possess some kind of biological activity beneficial to the organism. Phenolic compounds with healthy activity that are included in the scope of the invention are preferably polyphenols such as flavonols, anthocyanins and tannins, and more preferably resveratrol and quercetin forms.
    "Resveratrol" means 3, 5, 4-trihydroxy-trans-stilbene, a type of polyphenolic compound produced naturally by some plants.
    By "quercetin forms" is meant forms of the compound 2- (3, 4) -dihydroxyphenyl) -3, 5, 7-trihydroxy-4H-chromen-4-one, which is a flavonol that is found in high concentrations in both Fruits like vegetables. Although quercetin may be present in free form, its most frequent forms are linked to a molecule of a carbohydrate, specifically as O-glycoside, O-galactoside and O-rutinoside. Thus, examples of forms of quercetin that are included within the scope of the process of the invention, are preferably chosen from quercetin-3-O-glucoside, quercetin-3-O-galactoside and quercetin-3-O-rutinoside.
    “Activation agent” means that compound that when it interacts with a fruit
    or plant tissue activates or promotes the synthesis of other compounds existing in said material. Within the scope of the present invention, the activation agents are phytohormones existing in all higher plants, which are involved in growth, senescence and defense mechanisms against the attack of pathogens.
    P201430520
    04-08-2014
    Examples of red grapes, by way of illustration and not limitation, which are included in the scope of the process of the invention are Bobal, Cabernet Franc, Cariñena, Garnacha Ink, Merlot, Tempranillo and Malbec.
    5 The JM has two chiral centers at carbons 3 and 7 of the molecule. This implies that there may be four different stereoisomeric configurations, that is, as two pairs of different enantiomers. These configurations are called (-) - and (+) - JM ((3R, 7R) - and (3S, 7S) -isomers, respectively) and (-) - and (+) - methyl epijasmonate (epiJM, (3R , 7R) - and (3R, 7S) -isomers, respectively). As with all compounds
    10 chiral, the dissymmetric nature of certain biological receptors implies that the stereochemistry of JM is the main factor in the relationship between the structure of the molecule and its biological activity.
    The isolation of the enantiomers that are used in the process of the invention is
    15 performs, for example, starting from a stereoisomeric mixture of commercial JM, by preparative HPLC using a chiral column packed with permethylated ȕ-cyclodextrin as a stationary phase (see example 1). As one skilled in the art will know, it is possible to use any other technique that allows obtaining said enantiomers such as, for example, enantioselective synthesis.
    An example of a JM enantiomer that is used in the process of the invention is derived from a stereoisomeric mixture of commercial JM, comprising 5% of (-) - and (+) - epiJM and 95% of (-) - and (+) - JM and that is isolated by preparative HPLC using a chiral column packed with permethylated ciclo-cyclodextrin as stationary phase.
    The preferred ratio of JM enantiomer diluted in 1 ml of ethanol per gram of ink grape used in the process of the invention is between 0.005 and 0.1 μl.
    In a particular embodiment, the ratio of JM enantiomer diluted in 1 ml of ethanol per 30 grams of grape grapes is 0.025 μl.
    Preferably, the JM enantiomer is selected from (-) - JM and (+) - JM.
    The enantiomer that is used in the process of the invention comprises a high degree
    35 purity, which is preferably greater than 95%. However, enantiomers with lower degrees of purity are also included in the scope of the invention.
    P201430520
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    In another particular embodiment, the temperature used in step (b) of the process of the invention is 25 ° C and the period of time is 24 hours.
    Alternatively, the vial into which the JM enantiomer diluted in ethanol is introduced before starting step (c) of the process of the invention.
    In another particular embodiment, step (c) of the process of the invention is carried out for 5 days and at a temperature of 4 ° C.
    In another particular embodiment, the process of the invention comprising using an enantiomer that is (-) - JM and red grapes of the Red Globe variety, achieves an increase in resveratrol greater than 125%; of quercetin-3-O-glycoside greater than 350%; of quercetin-3-O-galactoside greater than 130%; and of quercetin-3-O-rutinoside greater than 125%, the percentages referring to the content of the untreated sample.
    In another particular embodiment, the process of the invention comprising using an enantiomer that is (+) - JM and red grapes of the Red Globe variety, achieves an increase of quercetin-3-O-glycoside greater than 75%; and of quercetin-3-O-rutinoside greater than 80%, the percentages referring to the content of the untreated sample.
    Throughout the description and the claims the word "comprises" and its variants are not intended to exclude other technical characteristics. For the person skilled in the art, other aspects, advantages and characteristics of the invention will be derived partly from the description and partly from the practice of the invention. The following figures and examples are
    25 provided by way of illustration, and are not intended to be limiting of the present invention.
    EXAMPLES OF EMBODIMENT OF THE INVENTION 30 Example 1. Isolation of JM enantiomers
    The pure enantiomers of JM: (-) - and (+) - of JM, were separated and isolated from the commercial compound formed by the stereoisomeric mixture, (Sigma-Aldrich; Steinheim, Germany) according to the procedure described in Flores et al. . (Food Chem., 2013, 141, 2982
    35 2987) which is based on preparative scale HPLC techniques and allows the four stereoisomers of JM to be chromatographed to baseline.
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    A 30 m long and 20 mm internal diameter column was used, packed with a thickness of 5 μm of permethylated ciclo-cyclodextrin, which was used as a chiral stationary phase. A solution of 50 mg of commercial JM in 10 ml of ethanol was started and 1500 μl of this solution was introduced into the chromatograph. He picked up a
    5 volume of 23.4 ml and 31.2 ml of the fractions of (-) - JM and (+) - JM respectively in the MeOH / H2O elution solvent and in independent vials. The isolated amounts of each of them were 3.56 mg respectively.
    The previous fractions were subjected to solid phase extraction (SPE) in reverse phase,
    10 using C18 as packing material and eluting with 2 ml of ethanol. The excess ethanol was evaporated in vacuo in a rotary evaporator to a final volume of 1 ml. In this way the four JM stereoisomers dissolved in ethanol were isolated. Specifically, 3.56 mg of (-) - and (+) - JM, respectively and 0.18 mg of (-) - and (+) - epiJM were collected. The purity with which they were isolated was 96.1%, 98.6%, 91.6% and 99.9% for (-) - JM, (-) - epiJM, (+)
    15 epiJM and (+) - JM, respectively.
    Example 2. Treatment of red grapes harvested using the method of the invention
    20 160 g of red grapes of the Red Globe variety were placed in a glass container of 1 L capacity, into which an open vial of 1 ml capacity was introduced. The container has a volume such that 2/3 of the container is occupied by red grapes and 1/3 is free to allow vaporization of the JM. Four different treatments were performed: the first by introducing 0.025 μl of the (-) - JM enantiomer diluted in 1 ml of ethanol
    25 in the vial; the second by introducing 0.025 μl of the (+) - JM enantiomer diluted in 1 ml of ethanol in the vial; the third by introducing 0.050 μl of the commercial stereoisomeric mixture into the vial, diluted in 1 ml of ethanol; the room without JM vial as a control.
    Each open glass container was placed inside an oven with the temperature
    30 thermostated at 25 ° C, which was maintained for 24 hours, leaving JM steam on the grapes. After this time, the JM enantiomer vial was removed from the container, sealed and stored at 4 ° C for 5 days.
    After the period, the grapes were lyophilized.
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    Example 3. Extraction of resveratrol and quercetin in treated and untreated red grapes
    Samples of the lyophilized grapes according to Example 2, were extracted with a mixture of MeOH / H2O in 80/20 proportion at room temperature using a blender for 5 min. For the extraction a volume of 20 ml of solvent per gram of sample was used. To ensure complete extraction of resveratrol and quercetin forms, the procedure was repeated twice. The two extracts obtained were combined, evaporating the solvent in vacuo using a rotary evaporator. The final dry extract was dissolved in MeOH for analysis by liquid chromatography.
    Example 4. Determination and quantification of bioactive compounds
    4.1. Resveratrol and quercetin forms in treated and untreated red grapes
    The extract according to example 3 was filtered using a 0.22 μm pore size filter. It was subsequently injected into HPLC using a 100 μl syringe. The equipment used was an LC Waters model 996, equipped with an automatic injector and diode array detector (DAD). The separation was carried out in reverse phase using a column of 250 mm length and 4.6 mm internal diameter and 5 μm phase thickness (C18, ACE, Madrid, Spain). A mixture of H2O with 1% formic acid (solvent A) and AcCN (solvent B) was used as the mobile phase. The applied flow was 1 ml / min throughout the analysis.
    The program used began with an isocratic composition of 5:95 of A: B during the 10 min of analysis to move to 10:90 over 15 min, at 15:85 in the next 10 min to finally finish in 25: 75 for the next 20 min. The final conditions were maintained for 10 min. Subsequently, it returned to the initial ratio of 5:95 which was maintained for 15 min to ensure cleanliness and stability between chromatographic analyzes. The signal was recorded at 304 and 348 nm to detect resveratrol and the three compounds derived from quercetin, respectively. To carry out the identification, a calibration line was prepared with model solutions between 0.00006 mg / l and
    0.25 mg / l. In all cases, retention times were compared with those provided by the standards under the same experimental conditions. An exception was quercetin-O-rutinoside, which had to be identified by mass spectrometry (MS), as described below, due to the lack of availability of the commercial standard.
    P201430520
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    The quantification of the four compounds was carried out by interpolating in the calibration line performed for each compound. Each injection was made in triplicate.
    4.2. Quercetin-O-rutinoside in treated and untreated red grapes
    5
    The extract according to example 3 was filtered with a 0.22 μm pore size filter and introduced into the liquid chromatograph. The equipment used was an Agilent Model 1100 LC equipped with two detectors, a DAD and an MS with electrospray interface.
    10 The separation was carried out in reverse phase using a 250 mm long column with 4.6 mm internal diameter and 5 μm phase thickness (C18, ACE, Madrid, Spain). A mixture of H2O with 1% formic acid (solvent A) and AcCN (solvent B) was used as the mobile phase. The applied flow was 1 ml / min throughout the analysis. The elution program used was the same as indicated in example 3. The spectra of
    15 masses were recorded in both positive and negative applying a voltage gradient from 200 m / z to 3000 m / z. The nebulizer pressure was set at 55 psi.
    4.3. Phenol concentration in treated and untreated red grapes
    20 The values obtained and the results of the statistical treatment of analysis of variances by ANOVA considering as significant differences those determined by the Student test, are shown in table 2.
    Table 2. Concentration of phenolic compounds with healthy biological activity present
    25 in the grape extract treated according to the process of the invention (μg of phenolic compound / g grape)
          Samples Resveratrol quercetin-quercetin-3-quercetin-33-O-O-galactoside O-rutinoside glycoside
    Untreated grapes (control) 27.4 ± 0.9 398.9 ± 0.7 58.9 ± 0.5 23.3 ± 0.6
    Grapes treated with the 22.3 ± 0.8 387.7 ± 0.5 21.5 ± 0.9 17.6 ± 0.3 commercial JM stereoisomeric mixture
    Grapes treated with (-) - JM 38.9 ± 1.0 807.6 ± 1.0 136.4 ± 0.8 43.6 ± 0.7
    Grapes treated with (+) - JM 21.5 ± 0.6 692.7 ± 0.7 58.9 ± 0.6 51.7 ± 0.8
    权利要求:
    Claims (11)
    [1]

    1. Procedure for simultaneously increasing the content of more than one phenolic compound with healthy biological activity in red grapes comprising:
    5
    a) contact the previously harvested red grapes with an enantiomer of Methyl Jasmonate (JM) diluted in ethanol.
    [2]
    2. Method according to claim 1, wherein the JM enantiomer diluted in ethanol is introduced into a vial and subsequently vaporized and contacted with the grapes.
    [3]
    3. Method according to any one of claims 1 and 2, wherein the red grapes and the JM enantiomer diluted in ethanol are introduced into a container that has a volume such that 2/3 of the container are occupied by the red grapes and 1/3 is free
    15 to allow vaporization of the JM.
    [4]
    4. Method according to any one of claims 1 and 3, which additionally comprises the following steps:
    20 b) subject the whole of step (a) to a constant temperature of between 25 and 40 ° C for a period of time between 20 and 30 hours; Y
    c) hermetically isolate the whole of stage (b) and keep it at a temperature between 4 and 10 ° C for a period of time between 0 and 7 days.
    5. Method according to any one of claims 1 to 4, wherein the JM enantiomer is used in a ratio between 0.005 and 0.1 µl diluted in 1 ml of ethanol per gram of grapes.
    6. Method according to any one of claims 1 to 5, wherein the JM enantiomer is used in a ratio of 0.025 μl diluted in 1 ml of ethanol per gram of grape.
    [7]
    7. Method according to any one of claims 1 to 6, wherein the JM enantiomer is selected from (-) - JM and (+) - JM.
    35
    13

    [8]
    8. Process according to any one of claims 1 to 7, wherein the JM enantiomer comprises a degree of purity greater than 95%.
    [9]
    9. Process according to any one of claims 1 to 8, wherein step (b) 5 takes place at a temperature of 25 ° C for a period of 24 hours.
    [10]
    10. Method according to any one of claims 1 to 9, wherein the vial is removed prior to step (c).
    11. Method according to any one of claims 1 to 10, wherein step (c) is carried at a temperature of 4 ° C for 5 days.
    [12]
    12. Process according to any one of claims 1 to 11, wherein the phenolic compounds are polyphenols.
    fifteen
    [13]
    13. Method according to any one of claims 1 to 12, wherein the polyphenols are resveratrol and quercetin forms.
    [14]
    14. Method according to any one of claims 1 to 13, wherein the forms 20 of quercetin are quercetin-3-O-glycoside, quercetin-3-O-galactoside and quercetin-3-Orutinoside.
    14
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    同族专利:
    公开号 | 公开日
    WO2015155387A1|2015-10-15|
    ES2550690B1|2016-09-06|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    ES2328002B2|2008-02-29|2010-03-29|Universidad De Alicante|COMBINED USE OF METHYL-JASMONATE AND CYCLODEXTRINES FOR RESVERATROL PRODUCTION.|CN108184990A|2018-02-09|2018-06-22|江苏沿海地区农业科学研究所|A kind of method for extending refrigeration cucumber freshness date using methyl jasmonate|
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    申请号 | 申请日 | 专利标题
    ES201430520A|ES2550690B1|2014-04-08|2014-04-08|PROCEDURE TO INCREASE THE CONTENT OF PHENOLS BIOLOGICAL CONNECTIVITY IN INK GRAPES THAT INCLUDES AN EXOGENOUS TREATMENT WITH A DILUTED METHOD JASMONATE ENANTIOMER|ES201430520A| ES2550690B1|2014-04-08|2014-04-08|PROCEDURE TO INCREASE THE CONTENT OF PHENOLS BIOLOGICAL CONNECTIVITY IN INK GRAPES THAT INCLUDES AN EXOGENOUS TREATMENT WITH A DILUTED METHOD JASMONATE ENANTIOMER|
    PCT/ES2015/070170| WO2015155387A1|2014-04-08|2015-03-11|Method for increasing the content of phenols with biological activity in red grapes, comprising an exogenous treatment with an enantiomer of methyl jasmonate diluted in ethanol|
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